In the past decades photochemistry of phthalimides developed into a fruitful field of research with many applications in synthesis. [1] In the context of our research of the synthesis of the adamantane derivatives with biological activity [2] we turned our attention to adamantane phthalimides. In this report we investigate photochemical H-activation reactivity of adamantane phthalimides 1-6 with the particular interest in domino reactions giving rise to polycyclic compounds (like 7, obtained as the only photoproduct from 1) with the potential anticancer activity.